Acid-Promoted Cyclization of α‑Azidobenzyl Ketones through CN Bond Formation: Synthesis of 6‑Substituted Quinoline Derivatives
An acid-promoted cyclization of α-azidobenzyl ketones has been developed for the synthesis of 6-substituted quinoline derivatives. A variety of synthetically useful 6-OTf or -OMs quinoline derivatives were obtained in moderate to good yields. The reaction proceeds via CN bond formation without orga...
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| Veröffentlicht in: | Organic letters 2024-01, Vol.26 (3), p.586-590 |
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| container_title | Organic letters |
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| creator | Zheng, Jing-Yun Luo, Ying Ou, Ting-Ting Zhang, Xin-Jie Lao, Yong-Qiang Feng, Na Peng, Jin-Bao Zhang, Xiang-Zhi Yao, Xiaojun Ma, Ai-Jun |
| description | An acid-promoted cyclization of α-azidobenzyl ketones has been developed for the synthesis of 6-substituted quinoline derivatives. A variety of synthetically useful 6-OTf or -OMs quinoline derivatives were obtained in moderate to good yields. The reaction proceeds via CN bond formation without organophosphine, providing convenient access to structurally interesting and synthetically important 6-substituted quinoline derivatives in moderate to good yields. A mechanistic perspective that is different from the traditional intramolecular Schmidt reaction has been proposed. |
| doi_str_mv | 10.1021/acs.orglett.3c03697 |
| format | Article |
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| source | American Chemical Society Journals |
| title | Acid-Promoted Cyclization of α‑Azidobenzyl Ketones through CN Bond Formation: Synthesis of 6‑Substituted Quinoline Derivatives |
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